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Mistress finally decided that she did indeed want the new bed. It will be delivered early next week.

Once it’s fully assembled, I’ll have to work on the larger under-bed drawer. It’s designed to be able to hold a moderate amount of clothing. It will need to be retrofitted to hold something else: me.

That’s a project that, thanks to my Y chromosome and my well outfitted workshop downstairs, shouldn’t be too challenging. Swap out the bottom for some 3/4″ plywood, reinforce all the corners with L-brackets, and install a generous quantity of low-profile wheels.

Mistress will also want some sort of way to lock it from the outside. Nothing fancy, since I won’t be able to reach it anyway. She’s also talked about some restraints in the drawer itself, but that’s probably an add-on for the future.

I’m actually fairly nervous about this. I do have some claustrophobia that kicks in sometimes. We haven’t really played that much with it. I’m a bit worried that I’ll have more trouble with that kind of panic now that I’ve fully transitioned from male to female. I’m just more emotionally volatile. One example is that I had to safeword on the severe bondage hood that I used to absolutely love to wear. It freaked me out.

The drawer itself is long enough to fit me (being about the length of the bed frame). There is also plenty of width — almost enough for two people. But the height is my biggest concern. Based on the dimensions, I think my nose will just barely rub as the drawer is opened and closed, unless I turn my head. Plus it will be dark.

Mistress talks fondly of “being able to just put me in the drawer for the night”. I hope I can live up to her expectations. This is really going to stretch me in some edgy ways.

She continues to talk to her close friend “Tom” about all sorts of intimate details of my surgery and my new genitals. She also mentions occasionally about the “openness in our relationship”, hinting strongly that we’d entertain the idea of having sex with others. And she’s talking seriously about us making a trip to see him early next year.

I’m still not healed well enough to get back to my spanking backlog. Mistress has given me some 200 swat penalties over the last month for transgressions. But I also was forgiven 150 last week for some substantial housework. I think my current outstanding total is 868. I’m trying hard to be a good girl!

Our relationship is back of firm ground. This gender transition has really stressed her out at times. But we are returning to some normality in our daily lives. And that makes a huge difference for her. I’m pretty sure now that our relationship will survive long-term, which utterly thrills me! When she and I are good, my universe is right and joyful. And right now, I’m so grateful to be living in that.

This is likely to be my last post as a biological male. Please feel free to follow my gender transition progress in more detail at my BloomingTime blog here on WordPress. When I next post, I’ll have traded my penis for a vagina. I’m quite excited to take this final step (Gender Confirmation Surgery)! In other news…

My wife / Mistress has been talking more about wanting heterosexual intercourse herself. My penis has not been functional (due to the feminizing hormones) for over year now. I, of course, desperately want her to be happy in all ways. So we keep talking about her having sex with men.

Even though I’m transitioning from male to female, I still want a woman for my LTR. However, I also love to have sex with men. Mistress knows this. She’s arranged for it before, and it will be up to her to decide what men will have me in the future. She also knows I have both rape and gang-bang fantasies.

Last week she sat me down so we could watch a few videos together. They were about swinging, something she’s done in the past (before we met). She also knows a couple who hosts swinging parties. At some point, once I’m fully healed (6 months?) she’s talked about arranging for us to both attend one of those parties. She’s even pondering us going to one of the larger swinging conventions/events. Wow.

Last weekend Mistress and I attended a BDSM play party for the first time in about a year. The location was new, and the dungeon was smaller. But there were a lot of people there we knew, which was awesome. We brought a friend for his first exposure to real-life, serious kinksters. We call him our “kinkling”. He got to see a few scenes and meet some great folks.

Although we brought two of our “toy bags”, Mistress had decided that we wouldn’t play with our kinkling present (it would be too awkward for all of us at this point). But she couldn’t help putting me into one scene when we came across one of the dungeon rooms.

Just off of the main dungeon was a little room. It had brick walls, and concrete for floor and ceiling. All it contained was a metal bed and mattress. But the mattress had an institutional 4-point restraint system at the ready. My knees got weak.

Institutional Restraint System

I’ve had fantasies about these kinds of restraints for decades, but I’d never experienced them personally. Mistress saw to that when she realized the effect they had on me.

Fully clothed, she had me lay down, and she quickly tightened them around my wrists and ankles. She kissed me on the forehead, smiled her evil smile, and left. I was “alone” and quickly determined that I could not reach any of the ties, so I literally could not escape. Easy and 100% effective full-body bondage.

Over the next 15 minutes, my mind went wild. I fast forwarded to being post-surgery, naked, and exposed to anyone. My ankles were apart, so I couldn’t close my legs. The feeling of vulnerability was stunning, and the fear this evoked surprised me. In my mind I was blindfolded or hooded and left as a plaything for whoever wanted to explore or use my body. At times I fought and thrashed and struggled against my bonds, of course to no avail.

I was sweating by the time Mistress returned and released me. It took me some time to get fully back to the present, it was that intense. She said she could see it in my eyes; she knows me well. I can’t imagine what the next time will be like. But she said I will certainly experience them again.

She also told me that a DM (dungeon monitor) talked to her as soon as she left me “alone”. She explained that she wanted me to think she was leaving me there (a mind-fuck she has used on me before), but that she would be keeping a close eye on me. I knew in this case that I was 100% safe, even if she had gone upstairs to mingle and munch with others. But it was nice to know that good dungeon safety protocols were being followed and enforced.

Just a reminder that everything in my blog is completely true. I am so thrilled to be living this life. I love my wife / Mistress with all my heart. Thanks for coming along on this journey with me.

I have a date for my surgery! In just 3 short months we will travel to the east coast. I’ll fall asleep with a penis and wake up with a vagina! I’m so thrilled and excited! OMG, I’ve waited so long for this!

Since we won’t be going to the west coast (as I blogged about last time), I won’t be able to see Ms. Dubois. And that’s a big bummer. I’m sure she could have provided some exquisite genital torture as “last rites” right before my surgery. But my wife/Mistress assures me that she will see that I do visit her dungeon for a very intense session sometime soon.

Those who have been following me here know that Mistress has teased me for years about her having sex with other men. And she often tells me fantasies about how she would involve me, sometimes just by being bound and having to watch her let another man make love to her.

Since we will soon have two vaginas in our household, she is making other plans. Over the last two weeks she’s come up with a list of four men (so far) that she says will help to “break in” my new parts. In other words, she’s going to turn me over to them for sex.

One of these men broke my man-cherry several birthdays ago (I should write a separate post about that sometime). She also initiated scenes with me and two of the other men at different times. One of the men has an even more wicked and kinky imagination than I do (which is rare!), so being at his mercy is sincerely frightening to me.

The fourth man is someone I mentioned two blog posts ago. Mistress has become good friends with him over the last year. He lives in a southern state, but travels internationally. She and “Tom” talk several times a day now. He was traveling nearby so we got to meet him a few weeks ago.

He told her about this village in Africa that he’s visited where the natives live very simply, including being nude all the time. They are very dark skinned, don’t speak english, and the men are tall and very muscular. She made a point of telling me that Tom said they are also all uncircumcised. Tom speaks many languages, including theirs.

Lately she has had this idea that, for my next birthday, she’ll send me with Tom to this village. Tom will let them know that the men can have their way with me. I envision these black giants passing me around like a rag doll, taking turns pleasuring themselves with me. Mistress can see by my intense blushing (which I can’t hide) that it’s tremendously erotic for me to think about.

Since it will take six months or so for me to heal after surgery, I would potentially be ready for intercourse sometime in April next year. Since my birthday is just a few months later, the timing seems like it would work. The way Mistress looks when she discusses this with me really makes me wonder if she is serious. I honestly think she might be.

She’s also made it clear that I won’t be the only one getting some male sexual attention around here. She’s talked about threesomes and foursomes, as well as her own special one-on-one time. Since she has been a swinger in the past, I don’t have any doubt that she would make good on any or all of that.

I’ve said it before, but I’ll mention it again. All of this is 100% true. This is my life. And I am utterly loving it. My Mistress is the best in the world — I love her with all my heart, and I know she loves me. Our relationship may sound weird to you, but neither of us would want it any other way.

We have a friend coming to visit next week. My wife / Mistress has been in contact with him for at least a year now, and they seem to be able to “talk about anything”. She teases me quite regularly about how she might offer me to him for sexual pleasure. He arrives Tuesday evening, and apparently is free most of Wednesday.

It could be that it will be a vanilla visit, with no sex involved. But he has included plenty of obvious innuendo in many of his emails and texts — my wife makes sure to show them to me. Although he’s married, he travels internationally a LOT, so who knows.

I’m nervous. I get the sense that my wife would be quite willing to be shockingly spontaneous, if the situation were right. Last week she asked me if I would be willing to do a three-way with her. I said yes, of course, but I still have a lot of emotional trepidation about it for real.

She also just let me know that one of my birthday presents will be arriving soon from Extreme Restraints. It won’t be the first or last time we’ve ordered from them.

I have a hood very similar to this one that they sell. I used to just love being in it – tight, sensory deprivation, locking, ultimate head bondage. But since my transition I have found that it’s a bit too frightening now. I’ve tried to put it on a few times, and I freak out. In all my decades of going deeper and deeper into bondage, that has never happened. I’m guessing it might have to do with the feminizing hormones, and my new emotional experience of the world.

I also think I might be within a week or two of selecting a surgeon for my GCS (gender-confirming surgery). I talked with five of them (or their office staff) extensively, getting dozens of my details questions answered. Remember that my wife is a nurse – no half-measures on this one. The list is down to two — one on each coast. One last call in just over a week, and it will be time for me to pick one and schedule a date to finally become physically female!

I’ve been living full-time as a woman for almost 14 months now, and I’ve been on feminizing hormones for even longer. One thing that means is that I can’t have penetrative sex anymore. To be blunt, my cock just won’t get hard enough for me to screw someone. Like my wife.

She loves to use this to humiliate me. This hormonally-induced impotence gives her lots of fodder for teasing. She doesn’t miss any opportunity to riff on words like limp, shriveled, tiny, ineffective, useless, etc.

She will also talk about being with other men for sex. I always – and I mean always – blush when she does. It’s involuntary. She’s even made be blush like that in front of friends, and they all find it humorous. Early on it seemed like she would talk about it just to tease. I’m not so sure anymore.

Yesterday our conversation turned to sex, and she asked me if I would like it if she were to have sex with a guy. I reluctantly said that I would understand, and that I wouldn’t mind. I said I sincerely wanted her to be happy. She asked me very specifically if that was my “final answer”. I said yes.

Tonight she told me she misses “man-sex”. I apologized for not being able to provide that for her any more. She said it didn’t matter, because she can get that whenever she wants, “Right?” I had to agree. After all, I honestly do want her to be fully sexually satisfied.

I know I can still satiate her sometimes. She lets me eat her out when she wants it. I never disappoint. But she says it’s not the same as a warm, firm penis inside her. I can’t dispute that.

I’ll be picking a surgeon this week for my Gender Conforming Surgery (which will convert my genitals from male to female). I think the finality of this is part of the energy that is going on.

I still can’t tell for sure if this “lesbian cuckolding” is something that she will go through with. More and more I am thinking that she will eventually. What’s unclear to me is whether she will get hers before or after she arranges for a man to take my newfound virginity. And I have no doubt at all that she will arrange that, if she hasn’t already.

My wife asked me today if I have ever been jealous, not just with her, but at all with anyone. I had to stop and think. And even then, I wasn’t sure.

My trust in her is so high, and we have such a strong relationship built on honesty and communication, that it’s truly never come up for me. Fidelity (or even flirting) in my previous marriage wasn’t an issue either.

So I find myself with about 30 years of married life and no real opportunities for me to feel jealous. Is that weird?

I also realized that my wife has never expressed significant interest in someone other than me. So it’s probably fair to say that we’ve never “gone there”.

The astute reader of my blog will recall that I’ve shared many stories here that my wife has told me about black men that she’s had sex with. They are great stories, and I see myself as a cuckold candidate because those stories turn me on. But they have always only been stories that she uses to humiliate me. After all, what kind of husband gets turned on hearing about his wife being unfaithful?

She took her questioning on the topic further, by asking flat out: “Do you think you’d feel jealous if I really did fuck another guy?” Again, I think it was weird that I had to think about my answer so much.

Eventually my answer was: “Well, if our relationship was threatened by it, then yes, I probably would feel jealous. But if it was just sex, well, probably not. It might also depend on whether or not I was present — but I’m not sure on that part.”

Many people have a strong connection between emotional intimacy and sexual intimacy. I’m like that in my primary relationship: if we’re emotionally struggling, I’m just not going to feel like having sex.

But my wife is not like that. She and a former husband, when they were married years ago, used to go to swingers parties. And yes, participate. But their relationship didn’t have the depth ours does. Swinging has not been a part of our time together.

My wife took it further. “So, if you came home one day and I told you I invited our friend Donny over, and rode his magnificent cock to several orgasms while you were at work, you wouldn’t be jealous?” Since I know that Donny doesn’t threaten our relationship at all, my only honest answer was “Well, no, I don’t think it would.”

“Hmmm….” she said teasingly, as she walked off towards her office (and her computer).

So my question for you is: now that I’m a female in a married lesbian relationship, could I still be considered a cuckold?

Things are still going well! I love being in the world as a woman now, instead of as a man. And unlike most married couples to find themselves wrestling with this issue (one partner being transexual), we are still going strong together. I think being openminded kinksters really helps.

I’m still eating out of my dog dishes, sometime 3 times a day. It’s so automatic now. My latest need for punishment has related to being tardy. My wife/mistress does not appreciate departing to an event with me when we are behind schedule. The last time we were 3 minutes late to meet some friends for dinner, she tacked on a penalty 5 minutes because I hurried through a yellow light (her opinion was that I ran a red light). That turned into a paddling with her favorite thick leather paddle, non-stop for the full eight minutes.

And she still has her appreciation for men of color. She rarely misses an opportunity to notice or comment on them, or even flirt with them. Humiliating me remains another past-time, making comments about my sexual inadequacy over the years as a man, and how my penis will be so much better off as a vagina anyway. There is little need for male chastity devices any more, as the female hormones have left tiny barely functional in that regard.

I can’t remember the last time she permitted me an orgasm. Several times per month, though, she instructs me to orally pleasure her, which I happily do. We both really enjoy that, and as a bonus she gets to ignore how horny it leaves me.

Our relationship is doing amazingly well, considering all we’ve been through lately. In many ways we feel closer than ever. And I’m extremely grateful for that. The next (and perhaps final) challenge for us will be the Gender Confirming Surgery (also known as SRS or GRS). She’s worried about infections and other problems. I’m still very excited to have my body fully reflect how I see myself now in the world – as a woman.

As time goes on, I’m less and less comfortable with my male genitals. They are inconvenient, as I cannot dress how I want sometimes. They are annoying, since tucking them snugly so they don’t bulge obviously under my clothes is a hassle. They hurt sometimes, as the atrophy fights with the occasional erection attempt. And mostly they no longer feel appropriate at all. I was in the shower with my wife, feeling horny, and instead of being able to rub my pussy against her thigh this damn semi-flaccid hunk of skin was flopping around. It honestly felt very wrong.

Electrolysis is a pain in the ass. I just completed my 7th trip to Dallas TX where they again removed all the active-growth hairs from my face. Eleven hours of technician time zapping and pulling those hairs one-by-one. Don’t mind the anesthetic injections — by needle into the face. Yeah, it really sucks. But most transitioning friends I know do it locally, without anesthetic, a half-hour or hour at a time. Which reminds me, I have to start that process in my genital area. It’s a strong recommendation prior to surgery down there. Apparently it’s quite painful too. So of course my wife wants to be with me during those procedures.

On the up side, I wore the cutest outfit to work yesterday! And heels, which I love. Actually, I only meant to do a brief post, as I need to be getting ready for work. Dress, jewelry, makeup, hair, and out the door.